Copper-Catalyzed Coupling of N -Phenoxyacetamides and 2H -Azirines for Synthesis of a-Amino Oxime Ethers

Copper-catalyzed coupling reaction involving N-phenoxy-acetamides and 2H-azirines is described, in which N-O and C-N bonds are broken and restructured. This protocol provides an efficient strategy for the highly regioselective synthesis of racemic ?-amino oxime ethers. In addition, this strategy can be used to modify natural products and is gram-scale compatible.

Automated summary

In this study, a copper-catalyzed coupling reaction between N-phenoxy-acetamides and 2H-azirines was investigated, involving the breaking and restructuring of N-O and C-N bonds. This protocol offers an efficient strategy for the regioselective synthesis of racemic ?-amino oxime ethers. Moreover, it is applicable for the modification of natural products and can be scaled up to gram quantities.